Champions League Debate: Who were greater - Manchester United 1999 or AC Milan 1989?

Two legendary teams - but which one comes out on top?

By Carlo Garganese

Beckham-Van Basten mix - Manchester United-Milan
When Manchester United won the treble in 1999, they certainly did it the hard way. The Premier League was recaptured, by one point, on the final day of the season. The Red Devils and the Gunners had gone toe-to-toe for almost the entire campaign, but an unlucky Arsenal defeat at Leeds in their penultimate game meant that a home win for United on the final day against Spurs would clinch the title. They went behind, but recovered to win 2-1.

The FA Cup conquest was even more dramatic. Although United won comfortably 2-0 in the final against Newcastle United, it was the semi-final against bitter rivals Arsenal that will live long in the memory. A thrilling match was tied at 1-1, United were down to 10 men after a Roy Keane sending off, and Nicolas Anelka had had a goal disallowed when Arsenal were awarded an injury time penalty to win the game. Peter Schmeichel saved brilliantly from Dennis Bergkamp, and then in extra time Ryan Giggs scored one of the greatest-ever solo goals to take United through. Many feel that if United had lost this game, Arsenal would have done the domestic double, and United would have won nothing.

Finally the Champions League itself. United’s run to the final could not have been any tougher. They progressed from a group involving Barcelona and Bayern Munich, saw off Inter in the quarter finals, and then defeated Juventus in another classic in the semis, having been 3-1 down in the tie at one point in the second leg.

The final itself was the icing on the cake. Trailing 1-0 early on to Mario Basler’s free kick, United were second best for almost the entire match, with Bayern twice hitting the woodwork, and Schmeichel making a number of crucial saves. Then, out of nowhere, substitutes Teddy Sheringham and Ole Gunnar Solskjaer both struck from corners in injury time to turn the tie on its head in the most dramatic of finishes. United were the treble winners, and champions of Europe for the first time since 1968.

As for Milan, they had endured arguably the worst spell in their history during the early 1980s as they were twice relegated to Serie B – once following the Totonero Scandal in 1980 and again in 1982 due to poor performances on the pitch. After a long dry spell, entrepreneur Silvio Berlusconi bought the club in early 1986 promising to restore former glories.

Berlusconi promptly bankrolled a spending spree as stars such as Marco van Basten, Ruud Gullit, Roberto Donadoni, Carlo Ancelotti joined the club along with a relatively unknown but tactically ground-breaking coach in Arrigo Sacchi. The Rossoneri won their first Scudetto in nine years in 1987/88 after a late Napoli collapse, and Milan further strengthened by snapping up a third Dutch superstar in Frank Rijkaard.

By the time 1988/89 arrived, Milan had become the best club team in the world and in addition to these aforementioned world class players, Sacchi perfected an almost impassable defence of Mauro Tassotti, Franco Baresi, Alessandro Costacurta and Paolo Maldini – regarded now as the best back four of all time.

After thrashing Bulgarians Vitosha 7-2 on aggregate in the European Cup first round, Milan would face their toughest tie on the way to 1989 glory in the second round against a Dragan Stojkovic and Dejan Savicevic inspired Red Star Belgrade. After a 1-1 draw at San Siro, Milan seemed to be on their way out as they trailed 1-0 to Savicevic’s goal in Belgrade and were also down to ten men. But, a heavy build up of fog saw the match abandoned past the hour mark and in the replayed game Milan won on penalties after a 1-1 draw.

Milan saw off Werder Bremen 1-0 in the last eight before one of the most famous nights in their history as they thumped Real Madrid 5-0 in the semi final home second leg after a 1-1 draw at the Santiago Bernabeu. In the final itself in Barcelona, two goals apiece from van Basten and Gullit saw the Rossoneri lift their first European Cup in 20 years by crushing Steaua Bucharest 4-0. Milan would go on to dominate European football over the next six years by reaching another four finals and winning two.

So who would win if Manchester United 1999 and Milan 1989 played one another? Goal.com takes a closer look…


Peter Schmeichel v Giovanni Galli

Ask many people who won United the treble in 1999, and they will answer Schmeichel. The Big Dane kept his side in the final at 0-1 with a string of great saves, produced miracles in the quarter final victory over Inter, and also stopped a last minute Dennis Bergkamp penalty in the FA Cup semi final that would have seen Arsenal through. A huge presence and arguably the best goalkeeper of the 1990s.

Giovanni Galli was a solid club shot-stopper, and kept clean sheets in the back-to-back successes in 1989 and 1990. Milan conceded just two goals in their last seven games. The next year Galli conceded just three in nine games, despite Bayern Munich and Real Madrid again being along the path. Much of the reason for this magnificent record was the legendary defence in front of him, and in truth Galli, who was Italy’s first choice at the 1986 World Cup, is regarded as the Azzurri’s weakest No.1 for decades.

1-0

Gary Neville v Mauro Tassotti

Neville was occasionally labelled as a weak-link of his team, and a player for the opposition to target before games. Nevertheless, despite his limitations, Neville never shirked a challenge, and has been a consistent performer over the years. His long career for club-and-country should also be praised.

Current Milan assistant coach Tassotti will sadly be best remembered for his brutal elbow on Spain’s Luis Enrique at the 1994 World Cup, but don’t let this cloud over what a world class defender he was. A no-nonsense right back, who was just as comfortable at centre back, Tassotti stayed at Milan during 17 thick and thin years spanning the entire 1980s and most of the 1990s. Forwards would wet themselves when up against the Roman-nosed hardman.

1-1

Jaap Stam v Franco Baresi


If there is one decision that Sir Alex Ferguson may regret during his long tenure at Old Trafford, it must surely be the decision to sell Jaap Stam in 2001. At the time, the Dutchman was among the best centre backs in the world, and one of the few who could really challenge the likes of Alessandro Nesta, Fabio Cannavaro and Lilian Thuram. Stam was fast, strong and powerful in the air and single-handedly held together an ordinary defence together in 1999.

Despite Stam’s brilliance, not even he gets anywhere close to the one and only Baresi, who is quite probably the best centre back in the history of football. The sweeper really did have it all. He was fast, good in the air, a perfect tackler, a born leader, a great starter of moves, and read the game like no one before or after him with countless interceptions. Baresi was the organiser of an almost impenetrable defence for club and country in 1989 and 1990.

1-2

Ronnie Johnsen v Alessandro Costacurta


A well respected player in Manchester during six years at the club, Johnsen was an unsung hero during the treble success in 1999. Indeed, he played a blinder during the famous semi-final comeback against Juventus in Turin. Nevertheless, like Scandinavian team-mate Henning Berg, who was once humiliatingly bamboozled by Real Madrid’s Fernando Redondo, you always felt that without Stam alongside him, he would have been susceptible.

Costacurta, on the other hand, despite having Baresi next to him, was a world class centre back in his own right. Such was his longevity that he retired at the age of 41 after 21 years at Milan. Like most top Italian defenders from the past Costacurta was a tactical master with faultless positioning, perfectly timed tackles and an elegant, breathless style of defending,

1-3

Denis Irwin v Paolo Maldini


Quiet on-and-off the pitch, I like to describe Irwin as the ‘Irish Gianluca Pessotto’. The reason for this is because, just like the Italian, he very rarely hit the headlines, but was a scarily consistent left back who seemingly was never taken on by the opposition winger. Irwin was excellent tactically, and a fine free kick and penalty taker, but he is never going to win a battle against the best left back of all time.

Maldini was the final piece of the meanest defence club football has ever seen. Spending his entire club career in the red and black number 3 shirt, Paolo spent a record-breaking 25 years in the first team. In that time, he won seven Serie A championships, one Coppa Italia, five Supercoppa Italiana, five UEFA Champions League's, five UEFA Super Cups, two Intercontinental Cups and one FIFA World Club Cup. All this, and the looks of a matinee idol.

1-4

David Beckham v Roberto Donadoni


In 1999, it is impossible to calculate just how many of Man Utd’s goals came from Beckham corners, crosses and free kicks. He is quite possibly the best crosser the game has ever seen, and played a key role in making the Red Devils such a powerful force during 12 years at Old Trafford from 1991-2003.

Donadoni was a truly world class winger, and one of Italy’s greatest ever. Milan beat Juventus to Donadoni’s signature in 1986 and over the next decade he won every major club honour in the game. A skilful and tricky wideman with brilliant technique, he also played 63 times for Italy, but is sadly most remembered for missing a crucial penalty in the semi-final shoot-out defeat to Argentina at Italia 90’.

1-5

Roy Keane v Frank Rijkaard


In the late 1990s, there were a number of world class defensive midfielders around – Edgar Davids, Didier Deschamps, Fernando Redondo, Patrick Vieira and, of course, Roy Keane. The Irishman was your typical midfield hardman, a sometimes unscrupulous figure, but a born winner. His box-to-box runs, and biting tackles, were a feature of the 1999 team, and he was crucial in the semi final comeback against Juventus.

Rijkaard was also a fantastic holding midfielder, who was just as world-class playing in defence. The Dutchman never received the recognition that his fellow countrymen in the Milan team, Gullit and Van Basten got. He won two Scudetti and two European Cups with the Rossoneri, scoring the winner against Benfica in the 1990 final. Rijkaard had it all – he was a physical beast but also technically brilliant.

1-6

Paul Scholes v Carlo Ancelotti


Now 35, the time will come when Paul Scholes hangs up his boots, and he will be sorely missed. Back in 1999, he was suspended for the final along with Keane, but his goals from midfield were vital in getting them there. His partnership and interchange with Keane was simply perfect. Scholes is still a force today but, due to age, he is naturally a level down from 11 years ago.

Ancelotti scored the opener in the famous 5-0 semi final second leg thrashing of Real Madrid in 1989, and was the calming influence in the Milan midfield. Carletto offered the experience and knowhow having reached the 1984 European Cup final with his beloved Roma only to be ruled out of the controversial penalty shootout defeat to Liverpool by injury.

2-6

Ryan Giggs v Angelo Colombo


Who can forget Giggs’ extra time winner against Arsenal in the 1999 FA Cup semi final? A goal that will be replayed for years and years. While Beckham provided the crosses from the right, Giggs sent his markers dizzy with his twisting runs down the left. The Welshman terrorised almost every player he came up against a decade ago, Inter’s Javier Zanetti being one of the few exceptions, and he was perhaps the best winger in the world at the time.

Colombo was not a winger, and is perhaps the only unknown outfield member of Sacchi’s great Milan team to your average fan. Yet the blonde-haired schemer played an unsung role in the Rossoneri midfield, working tirelessly and winning the ball for his more talented team-mates.

3-6

Dwight Yorke v Ruud Gullit


Yorke was a goal-machine for a few years at the turn of the millennium. As well as his partnership with Andy Cole, the ‘Smiling Assassin’ scored numerous headers from Beckham crosses, and rarely missed when presented with a chance. The Trinidad and Tobago frontman was also intelligent and was good at bringing team-mates into play.

But Yorke is not even close to being on the same level as the powerful Ruud Gullit. The dreadlocked Dutchman was a quite imposing physical specimen with frightening explosiveness and power. He forged an unstoppable forward partnership with Marco Van Basten, scoring twice in the 1989 final, but also often played on the wing and wide midfield.

3-7

Andy Cole v Marco van Basten


Cole had fine movement and penalty box intelligence, but his finishing often left a lot to be desired. If he had been more clinical, his goal tally would have broken records because it was already prolific enough. His link-up play with Yorke was telepathic - the dummy, step-over and return-pass routine was the pair’s trademark on the way to sharing 53 goals in 1998/99.

One of the game’s most complete forwards, Van Basten was the final piece of the famous Dutch triad. He won the Ballon d’Or and the Scudetto three times respectively, the European Cup twice and scored 108 goals in 168 matches for the club. During 1988/89 he scored in every round, including two in the final against Steaua, two in the semi final against Real Madrid, and four in one match versus Vitosha. Right foot, left foot, with his head, Van Basten was the best. Retired at the age of 29 due to injury.


FINAL SCORE: Manchester United 1999 3-8 AC Milan 1989



What are your views on this topic? Who were greater – Manchester United 1999 or AC Milan 1989? Goal.com wants to know what YOU think…


 
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